102123-74-0

Basic information

• Product Name: (3S)-3-(tert-Butoxycarbonyl)amino-1-chloro-4-phenyl-2-butanone
• Synonyms: Carbamic acid,N-[(1S)-3-chloro-2-oxo-1-(phenylmethyl)propyl]-, 1,1-dimethylethyl ester;(3S)-3-(N-Boc-amino)-1-chloro-4-phenyl-2-butanone;(3S)-3-(tert-Butoxycarbonyl)amino-1-chloro-4-phenyl-2-butanone;Carbamic acid, [(1S)-3-chloro-2-oxo-1-(phenylmethyl)propyl]-, 1,1-dimethylethyl ester (9CI);N-[(1S)-3-chloro-2-oxo-1-(phenylmethyl)propyl]-Carbamic acid 1,1-dimethylethyl ester;N-[(1S)-3-chloro-2-oxo-1-(phenylMethyl)propyl]-;(S)-tert-Butyl (4-chloro-3-oxo-1-phenylbutan-2-yl)carbaMate
• CAS NO: 102123-74-0
• Molecular Formula: C₁₅H₂₀ClNO₃
• Molecular Weight: 297.78
• EINECS: 1312995-182-4
• Mol File: 102123-74-0.mol
• Article Data: 26

Chemical Properties

• Melting Point: 103 °C
• Boiling Point: 423.882 °C at 760 mmHg
• Flash Point: 210.157 °C
• Appearance: /
• Density: 1.15 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.517
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 10.94±0.46(Predicted)
• CAS DataBase Reference: (3S)-3-(tert-Butoxycarbonyl)amino-1-chloro-4-phenyl-2-butanone(CAS DataBase Reference)
• NIST Chemistry Reference: (3S)-3-(tert-Butoxycarbonyl)amino-1-chloro-4-phenyl-2-butanone(102123-74-0)
• EPA Substance Registry System: (3S)-3-(tert-Butoxycarbonyl)amino-1-chloro-4-phenyl-2-butanone(102123-74-0)

Safety Data

• Hazardous Substances Data: 102123-74-0(Hazardous Substances Data)

Usage

General Description

The chemical "(3S)-3-(tert-Butoxycarbonyl)amino-1-chloro-4-phenyl-2-butanone" is a compound containing a chlorine atom attached to a butanone moiety, with a phenyl group and a tert-butoxycarbonyl amino group. It has a chiral center at the third carbon, with the S configuration. (3S)-3-(tert-Butoxycarbonyl)amino-1-chloro-4-phenyl-2-butanone is commonly used in organic synthesis and medicinal chemistry as a building block for creating more complex molecules. It is also used in research as a starting material for the preparation of various pharmaceuticals and bioactive compounds. Additionally, it may have potential pharmaceutical applications due to its structural characteristics.

InChI:InChI=1/C15H20ClNO3/c1-15(2,3)20-14(19)17-12(13(18)10-16)9-11-7-5-4-6-8-11/h4-8,12H,9-10H2,1-3H3,(H,17,19)/t12-/m0/s1

Upstream product

• 593-71-5 Chloroiodomethane 
• 4522-04-7 ethyl N-{[(1,1-dimethylethyl)oxy]carbonyl}-L-phenylalaninate 
• 51987-73-6 (S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 290836-37-2 (3S)-3-tert-butoxycarbonylamino-1,1-dichloro-4-phenyl-2-butanone 
• 60398-41-6 (3S)-tert-butyl 1-benzyl-3-diazo-2-oxopropylcarbamate 
• 85613-64-5 (S)-3-(tert-butoxycarbonyl)amino-4-phenyl-2-butanone 
• 186581-53-3 diazomethane 
• 67729-36-6 Boc-Phe-O-COO-isoBu 
• 286019-77-0 (3S)-1-chloro-3-(diphenylmethylene)amino-4-phenyl-2-butanone 
• 339190-43-1 N-benzylidene (S)-phenylalanine methyl ester 
• 120238-42-8 methyl (S)-2-(diphenylmethylideneamino)-3-phenylpropanoate 
• 7535-56-0 N-t-butoxycarbonyl-L-phenylalanine 4-nitrophenyl ester 
• 400611-25-8 tert-butyl (S)-(4-(dimethyl(oxo)-λ6-sulfanylidene)-3-oxo-1-phenylbutan-2-yl)carbamate 

Downstream Products

• 152438-66-9 Boc-Phe-4-acetylphenoxymethyl ketone 
• 165727-45-7 tert-butyl ((2S,3S)-4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbamate 
• 1026473-02-8 {(S)-5-[(S)-2-((S)-3-tert-Butoxycarbonylamino-2-oxo-4-phenyl-butylamino)-3-phenyl-propionylamino]-5-carbamoyl-pentyl}-carbamic acid benzyl ester 
• 1027306-89-3 ((S)-1-Benzyl-3-{(S)-1-[(S)-2-(2-benzyloxycarbonylamino-ethylcarbamoyl)-1-carbamoyl-ethylcarbamoyl]-2-phenyl-ethylamino}-2-oxo-propyl)-carbamic acid tert-butyl ester 
• 162536-40-5 (2R,3S)-1-Chloro-2-hydroxy-3-N-(tert-butoxycarbonyl)amino-4-phenylbutane 
• 923601-69-8 (1R,2S)[3-chloro-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid 1,1-dimethylethyl ester 
• 98760-08-8 (2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane 
• 98760-08-8 (1-oxiranyl-2-phenylethyl)carbamic acid tert-butyl ester 
• 169280-56-2 4-amino-N-(2R,3S)(3-amino-2-hydroxy-4-phenylbutyl)-N-isobutylbenzenesulfonamide 
• 206361-99-1 darunavir 
• 160232-08-6 (2R,3S)-3-tert-butoxycarbonylamino-1-isobutylamino-4-phenyl-2-butanol 
• 191226-98-9 [(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester 
• 162539-71-1 {(1S,2R)-1-Benzyl-3-[((S)-3-tert-butoxycarbonylamino-2-oxo-4-phenyl-butyl)-methyl-amino]-2-hydroxy-propyl}-carbamic acid tert-butyl ester 
• 34351-19-4 (3S)-3-amino-1-chloro-4-phenyl-2-butanone hydrochloride 

Relevant articles and documents

Design and Optimization of a Continuous Stirred Tank Reactor Cascade for Membrane-Based Diazomethane Production: Synthesis of α-Chloroketones

The development of a continuous diazomethane generator comprising a continuous stirred tank reactor (CSTR) cascade and membrane separation technology is reported. This reactor concept was applied for the telescoped three-step synthesis of a chiral α-chloroketone, a key building block for many HIV protease inhibitors, via a modified Arndt-Eistert reaction starting from N-protected l-phenylalanine. The initial mixed anhydride was generated in a coil reactor and directly introduced into the CSTR diazomethane cascade. The use of a semipermeable Teflon membrane (AF-2400) allowed the generation of anhydrous diazomethane, which diffuses through the membrane into the CSTR where it is immediately consumed by the anhydride to furnish the corresponding diazoketone. The subsequent halogenation with concentrated HCl was performed downstream in batch and allowed production of the α-chloroketone on a multigram scale, with a productivity of 1.54 g/h (5.2 mmol/h).

Practical synthesis of α-aminoalkyl-α′-chloromethylketone derivatives. Part 2: Chloromethylation of N-imine-protected amino acid esters

Chloromethylation of N-imine-protected amino acid esters followed by acid hydrolysis gave α-aminoalkyl-α′-chloromethylketone as a HCl salt form in good yield without racemization. The amino group was conveniently protected with carbamate protecting reagents to give various useful intermediates for the protease inhibitors.

SULFOXONIUM YLIDE DERIVATIVES AS PROBES FOR CYSTEINE PROTEASE

The present invention relates to compounds of formula I bearing a sulfoxonium ylide moiety as warhead, or salts thereof. Such compounds can be used as activity-based probes for cysteine proteases such as cathepsin X, in methods of detecting cysteine protease activity and in related diagnostic or therapeutic methods.

4-amino-N-[ (2R, 3S) - 3-amino-2-hydroxy-4-phenyl-butyl]-N- isobutyl-benzene sulfonaide preparation method

The invention discloses a method for preparing 4-amino-N-[(2R,3S)-3-amino-2-hydroxy-4-benzene butyl]-N-isobutyl benzsulfamide. The method comprises the following steps: S1: enabling L-phenylalanine and diazomethane to react to obtain a diazo methyl ketone intermediate product, and enabling the diazo methyl ketone intermediate product and haloid acid to react to obtain a compound A; S2, conducting carbonyl deoxidation on the compound A to obtain a compound B; S3, under the existence of iso-butylamine, conducting cyclization reaction and ring-opening reaction on the compound B in sequence to obtain a compound C; S4, enabling the compound C and nitrobenzenesulfonyl chloride to react to obtain a compound D; S5, conducting nitro reduction on the compound D to obtain the 4-amino-N-[(2R,3S)-3-amino-2-hydroxy-4-benzene butyl]-N-isobutyl benzsulfamide. The method is simple in course, low in cost, mild in condition, and higher in intermediate product stability, and is beneficial for industrial application.